Hydrochloric Acid → HCID 58137752, compound

HRID 2189457Notes

Reaction equation

[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8]C(C)(C)C)=[O:7])=[CH:4][CH:3]=1.Cl[C:16]1[S:17][C:18]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:19]=2[N:20]=1.Cl.O1CCOCC1>C(O)(C)C>[Cl:25][C:23]1[CH:22]=[CH:21][C:19]2[N:20]=[C:16]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:13][CH:14]=3)[S:17][C:18]=2[CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of tert-butyl 4-aminobenzoate (6.36 g, 32.9 mmol) and 2,6-dichlorobenzothiazole (5 g, 24.5 mmol) in isopropanol (150 mL) was added 4 N HCl in 1,4-dioxane (4 mL, 16 mmol). The mixture was refluxed at 100° C. for 7 h, and then allowed to cool to room temperature. White precipitates formed during cooling were isolated by filtration to yield the first crop of the title compound as a white solid (3.13 g). The filtrate was concentrated in vacuo and then stirred in a mixed solvent of TEA (20 mL) and CH2Cl2 (20 mL) overnight. The solvent was removed in vacuo, and the residue was triturated with isopropanol/ethyl acetate. The isolated white solid was stirred in a mixed solvent of isopropanol (12 mL) and ethyl acetate (8 mL) for 0.5 h and collected by filtration to yield the second crop of the title compound (3.5 g) (total 6.63 g, 85% yield). HPLC/MS (Method C): retention time=2.51 min, [M+H]+=305.3. 1H NMR (500 MHz, DMSO-d6) δ 11.08 (bs, 1H), 7.98 (d, J=2.20 Hz, 1H), 7.94 (m, 2H), 7.88 (m, 2H), 7.64 (d, J=8.25 Hz, 1H), 7.36 (dd, J=8.80, 2.20 Hz, 1H).

Workup

temperatureto cool to room temperature
customWhite precipitates
customformed
temperatureduring cooling
customwere isolated by filtration

Sources & evidence

ORD record: ord-5ebe5c44b5a3439b90d2f36fc737849f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324241B2

Reaction notes

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